L-Hydroxyproline → (2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid

HRID 1006803노트

반응식

HRID 1006803 반응식
[NH:1]1[CH2:9][C@H:7]([OH:8])[CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(N1CCOCC1)C.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C[Si](C)(C)N[Si](C)(C)C.C1COCC1.CCOCC.C(O)C>[OH:8][C@H:7]1[CH2:9][N:1]([S:28]([C:19]2[CH:20]=[CH:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)(=[O:30])=[O:29])[C@H:2]([C:3]([OH:5])=[O:4])[CH2:6]1

참가 물질

9

반응물 4

HCID 5810L-HydroxyprolineHCID 71252-Naphthalenesulfonyl chlorideHCID 7525EthylmorpholineHCID 516892Sodium Bicarbonate

생성물 1

HCID 6363699(2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid수율 67.9%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 13838Hexamethyldisilazane용매

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온도
120 °C

실험 절차

11 g (83.9 mmol) L-Hydroxyproline were dissolved in 110 ml hexamethyldisilazane and heated to 120° C. overnight, cooled to room temperature and evaporated. The oily residue was dissolved in 110 ml THF, 16.5 ml (79.7 mmol, 0.95 eq) N-ethyl-morpholine was added, followed by 18.25 g (79.7 mmol, 0.95 eq) 2-naphthalenesulfonyl chloride in 130 ml THF over a period of 60 min. The solution was stirred at RT for 50 h, 15 ml ethanol were added and the solution was stirred for 15 min. At that time 400 ml of Et2O and 250 ml of aqueous saturated NaHCO3 solution were added and the phases were separated. The aqueous layer was acidified and extracted with EtOAc, the combined organic layers were washed with brine, dried over MgSO4 and concentrated. 17.39 g (65%) (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid isolated as yellow solid, mp 140° C., MS: 321 (MH+).

후처리

  1. temperaturecooled to room temperature
  2. customevaporated
  3. dissolutionThe oily residue was dissolved in 110 ml THF
  4. stirringthe solution was stirred for 15 min
  5. customthe phases were separated
  6. extractionextracted with EtOAc
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6e9d53e4d07741a38af4142a10c1cf24
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790860B2

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